Benzoyl chloride → glucopyranose pentabenzoate

HRID 987940Notes

Reaction equation

HRID 987940 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.O>[C:13]([O:1][CH:2]1[O:10][C@H:9]([CH2:11][O:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:7]([O:8][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:5]([O:6][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:3]1[O:4][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 11456758glucopyranose pentabenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

100 g of D-glucose (555 mmol; 1 eq) are dissolved in 2 l of pyridine and the reaction medium is heated under reflux for 1 hour before 387 ml (3,330 mmol; 6 eq) of benzoyl chloride are added thereto in the hot. After addition, the medium is diluted with water, the product precipitates and is filtered off and rinsed with water to neutrality. After drying, it is purified by recrystallisation from ethyl acetate.

Workup

  1. temperaturethe reaction medium is heated
  2. additionare added
  3. additionAfter addition
  4. customthe product precipitates
  5. filtrationis filtered off
  6. washrinsed with water to neutrality
  7. customAfter drying
  8. customit is purified by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-943c3a5f4c9e4fe7b8b657c828aace41
Source dataset
uspto-grants-2003_10
Patent number
US06632940B1

Reaction notes

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